3,4-dihydro-2H-pyran → 5-Bromo-2-t-butyl-1-(2-tetrahydropyranoxy)benzene

HRID 377344Notes

Reaction equation

HRID 377344 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)=[C:4]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:3]=1.[Br:19]C1C=CC(C(C)(C)C)=C(O)C=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O1C=CCCC1>ClCCl>[Br:19][C:7]1[CH:2]=[CH:3][C:4]([C:15]([CH3:18])([CH3:17])[CH3:16])=[C:5]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:6]=1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 103313825-Bromo-2-tert-butylphenol2×HCID 158188564-Bromo-2-t-butyl-1-(2-tetrahydropyranoxy)benzene2×

Product 1

HCID 226203655-Bromo-2-t-butyl-1-(2-tetrahydropyranoxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the same procedure as for the preparation of 4-bromo-2-t-butyl-1-(2-tetrahydropyranoxy)benzene (Compound H), but instead using 8.18 g (35.7 mmol) of 5-bromo-2-t-butylphenol (Compound D), 0.90 g, 3.6 mmol) of pyridinium p-toluenesulfonate and 4.50 g (4.9 ml, 53.6 mmol) of 3,4-dihydro-2H-pyran and 50 ml of dichloromethane stirred at room temperature for 21 hours produced a dark yellow solution. At this time an additional 1.80 g (7.2 mmol) of pyridinium p-toluenesulfonate was added to the solution and it was allowed to stir at room temperature for 19 hours. After aqueous workup a clear, yellow oil was isolated. Purification by flash chromatography (silica, 5% ethyl acetate in hexane) yielded the title compound as a clear, slightly yellow oil. PMR (CDCl3): d 1.38 (9H, s), 1.6-2.1 (6H, m), 3.65-3.75 (1H, m), 3.8-3.95 (1H, m), 5.45 (1H, t, J=2.5 Hz), 7.03 (1H, dd, J=8.4, 2.0 Hz), 7.13 (1H, d, J=8.4 Hz), 7.33 (1H, d, J=2.0 Hz).

Workup

  1. customproduced a dark yellow solution
  2. stirringto stir at room temperature for 19 hours
  3. customAfter aqueous workup a clear, yellow oil was isolated
  4. customPurification by flash chromatography (silica, 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b5526a6034234626a10201daff7588bf
Source dataset
uspto-grants-2000_02
Patent number
US06025388

Reaction notes

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